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On the Reactivity of Ferrocenoylsilanes
Author(s) -
Bonini Bianca F.,
ComesFranchini Mauro,
Fochi Mariafrancesca,
Mazzanti Germana,
Ricci Alfredo,
Alberti Angelo,
Macciantelli Dante,
Marcaccio Massimo,
Roffia Sergio
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(20022)2002:3<543::aid-ejoc543>3.0.co;2-r
Subject(s) - chemistry , reactivity (psychology) , aldehyde , reagent , lithium (medication) , hydride , aluminum hydride , lithium aluminium hydride , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , medicine , hydrogen , alternative medicine , pathology , methoxide , endocrinology
Reactions of ferrocenoylsilanes 1 with lithium aluminium hydride and organometallic reagents show unusual behaviour in that the ferrocenyl aldehydes 4 and ketones 5−9 are obtained instead of the expected secondary and tertiary silylated alcohols. This paper also reports on the synthesis and reactivity of the first planar chiral enantiomerically pure ferrocenoylsilane 1d that offers the possibility of synthesizing planar chiral enantiomerically pure 1,2‐disubstituted aldehyde 4b and ketones 5b , 6b , 7b , 8 and 9 . A mechanistic hypothesis is proposed for explaining the obtained results.